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Have a Fling in the Florida Keys

The Florida Keys are a little wilder, a little bit beyond the typical Florida scene and perhaps a little closer to what you’re looking for in a romantic - yet not too distant - escape. You don’t have to worry about passports or language barriers down here; these islands may feel far away but they have a way of feeling like home, too. Thanks to the abundance of Florida Keys vacation rentals scattered about like so many conch shells, you can truly have it all as you finally treat yourself to a getaway built for two.


In Islamorada, Key Largo, Marathon and Key West (that’s just for starters) there are beach houses, condos, villas and cottages for everyone. You and your partner in crime (not that it should be deemed illegal to steal a long weekend and just enjoy yourselves) can take your pick from among luxury digs and modest love nests alike; head for a stretch of shoreline hopping with clubs and tiki bars or hide away on your own little island – literally.


Weigh your options, talk it over with your lucky companion and see how the scenario develops. Activities will range from diving and snorkeling to drinking and dancing, nodding off on the beach to nodding off next to your private pool…you set the schedule and itinerary as you please. You won’t be able to control the time of the sunset – or your amazement at its brilliance – but other than that the strings are yours to pull.


A popular place for weddings, honeymoons and lovey-dovey rendezvous, you’ll soon feel the good vibes for yourself. Maybe it’s the island culture, maybe it’s the chance to have the whole house to yourself; the point is, this trip will be good for you both.

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  1. Futura Yacht Club
    Tropically Furnished Condo with Ocean Views — Property 301565

    Vacation Condo rental in Florida Keys area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • tennis court
    Discount $50.00 Off Weekly Rate
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $750 - $1000 per property per week

  2. Oceanfront, Tremendous Sunrise
    New Oceanfront, w/ Breathtaking views - 5 Star Resort - Huge Lagoon Pool — Property 129473

    Vacation Condo rental in Key Largo area
    • Condo
    • 2 bedrooms , sleeps 10
    • 2 bathrooms
    • 1 half bathroom
    • resort, waterfront
    • daily maid service
    Fall / Winter / Spring Special!!!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1495 - $2995 per property per week

  3. 5th Floor Oceanfront End Unit!
    Oceanfront 5th Floor End Unit! Pool, Internet, Tennis, Panoramic Ocean Views — Property 151910

    Vacation Condo rental in Islamorada area
    • Condo
    • 2 bedrooms , sleeps 5
    • 2 bathrooms
    • beach, waterfront
    • sauna
    Christmas Week, $50 Discount
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $800 - $1500 per property per week

  4. Secret Garden in Key West — Property 168086

    Vacation Condo rental in Key West area
    • Condo
    • 2 bedrooms , sleeps 4
    • 1 bathroom
    • downtown, near the ocean
    • pool
    Nov. and Dec. special rate $975 per week
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $950 - $1900 per property per week

  5. Tad's Place
    Owner Operated Waterfront Vacation Rental — Property 106890

    Vacation Condo rental in Key Colony Beach area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • waterfront
    • pool
    800.00 Special
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $800 - $1100 per property per week

  6. Waterfront Luxury in Old Town Key West — Property 166032

    Vacation Condo rental in Key West area
    • Condo
    • 1 bedroom , sleeps 5
    • 1 bathroom
    • resort, waterfront
    • fitness room
    Rates (shown in USD)
    $1595 - $2750 per property per week

  7. Ocean and Sunset View in Gorgeous Truman Annex — Property 244472

    Vacation Condo rental in Key West area
    • Condo
    • 2 bedrooms , sleeps 4
    • 1 bathroom
    • near the ocean, town
    • pool
    Rates (shown in USD)
    $1200 - $1800 per property per week

  8. Pelican's Perch
    Oceanfront (Gulf) Condo, Fabulous Views, Heated Pool & Dock — Property 113802

    Vacation Condo rental in Marathon area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • 1 half bathroom
    • near the ocean, waterfront
    • pool
    Rates (shown in USD)
    $986 - $1586 per property per week

  9. Sea Gulls Condominium
    Spectacular Oceanfront View Condo Newly Remodeled — Property 255809

    Vacation Condo rental in Tavernier area
    • Condo
    • 1 bedroom , sleeps 2
    • 1 bathroom
    • village, waterfront
    • pool
    Rates (shown in USD)
    $800 - $950 per property per week

  10. Luxury Waterfront at the Galleon Resort in Old Town — Property 161268

    Vacation Condo rental in Key West area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • resort, waterfront
    • balcony
    Rates (shown in USD)
    $2350 - $4150 per property per week

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